Various phenylcarbamoylbenzimidates were prepared in conjunction with a study on the structure of carbamoylamidoximes by R. Boyle, et al., Helv. Chim. Acta, 46, 1073 (1963).
Various 2,6-difluoro-benzoylimidates, including ethyl 2,6-difluoro-N-[[[4-(2-chloro-4-trifluoromethylphenoxy)phenyl]amino]carbon yl]benzenecarboximidate, are described as insecticides especially effective against lepidopterous and coleopterous insects in European Patent Application Number 79300868.1 filed May 18, 1979 and published Dec. 12, 1979 with a Publication Number: 0 005 944. See also U.S. Pat. No. 4,200,653.
Various benzoylureas have been described in the literature and patents as insecticides including those described in U.S. Pat. Nos. 3,748,356, 4,103,022, 4,160,834, 4,170,657 and others.
U.S. Pat. No. 3,992,553 describes various benzoylureido-diphenyl ethers as insecticides, including:
4-nitro-2',6'-dichloro-4'-[N-(N'-(2-chlorobenzoyl))-ureido]-diphenyl ether, PA0 3-chloro-4-cyano-2'-chloro-4'-[N-(N'-(2-chlorobenzoyl))-ureido]-diphenyl ether, PA0 3-chloro-4-nitro-2'-chloro-4'-[N-(N'-(2-chlorobenzoyl))-ureido]-diphenyl ether, and PA0 4-cyano-2',6'-dichloro-4'-[N-(N'-(2-chlorobenzoyl))-ureido]-diphenyl ether. PA0 Ethyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzene carboximidate, PA0 Ethyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzene carboximidate, PA0 Ethyl 2,6-dichloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Ethyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluoroben zenecarboximidate, PA0 Ethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluorobenzene carboximidate, PA0 Ethyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzene carboximidate, PA0 Ethyl N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluo robenzenecarboximidate, PA0 Ethyl 2-chloro-N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarb oximidate, PA0 1-Methylethyl 2-chloro-N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarb oximidate, PA0 Ethyl N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-di fluorobenzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Ethyl 2-chloro-N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbony l]benzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzene carboximidate, PA0 1-Methylethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-dichlorobenzene carboximidate, PA0 Ethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzenecarb oximidate, PA0 Ethyl 2,6-difluoro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Ethyl 2-chloro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]carbony l]benzenecarboximidate, PA0 Ethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzenecarb oximidate, PA0 Ethyl 2-chloro-N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]be nzenecarboximidate, PA0 Ethyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-dichlo robenzenecarboximidate, PA0 Ethyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobe nzenecarboximidate, PA0 Ethyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbe nzenecarboximidate, PA0 Methyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzene carboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]2-fluorobenzenec arboximidate, PA0 Methyl 2,6-dichloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]2,6-difluorobenz enecarboximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluorobenzene carboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzene carboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluo robenzenecarboximidate, PA0 Methyl 2-chloro-N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarb oximidate, PA0 Methyl N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-di fluorobenzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Methyl 2-chloro-N-[[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbony l]benzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzene carboximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzenecarb oximidate, PA0 Methyl 2,6-difluoro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Methyl 2-chloro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]carbony l]benzenecarboximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzenecarb oximidate, PA0 Methyl 2-chloro-N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]be nzenecarboximidate, PA0 Methyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-dichlo robenzenecarboximidate, PA0 Methyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobe nzenecarboximidate, PA0 Methyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluo robenzenecarboximidate, PA0 Methyl N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbe nzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-(nitrophenoxy)-phenyl]amino]carbonyl]benzenecarboximid ate, PA0 1-Methylethyl 2,6-dichloro-N-[[[3,5-dichloro-4-(3-chloro-4-cyanophenoxy)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Ethyl 2-chloro-N-[[[4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarboximidate PA0 1-Methylethyl 2-chloro-N-[[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]amino]carbonyl]be nzenecarboximidate, PA0 Methyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzene carboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzene carboximidate, PA0 Methyl 2,6-dichloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluoroben zenecarboximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluorobenzene carboximidate, PA0 Methyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzene carboximidate, PA0 Methyl 2-chloro-N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarb oximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-dichlorobenzene carboximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzenecarb oximidate, PA0 Methyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzenecarb oximidate, PA0 1-Methylethyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzene carboximidate, PA0 1-Methylethyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzene carboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 1-Methylethyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluoroben zenecarboximidate, PA0 1-Methylethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2,6-difluorobenzene carboximidate, PA0 1-Methylethyl N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzene carboximidate, PA0 1-Methylethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-fluorobenzenecarb oximidate, PA0 1-Methylethyl N-[[[3-chloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]-2-methylbenzenecarb oximidate.